Cosmetic or dermatological composition comprising a merocyanine and a thiopyridinone compound

Abstract

Title: Cosmetic or dermatological composition comprising a merocyanin and a Thiopyridinone compound The present invention relates to a cosmetic or dermatological composition comprising at least one aqueous phase, at least one merocyanin of formula (3) which will be defined in detail later and at least one compound of formula (I) or (I'), as described below, and / or their optical isomers, geometric isomers as well as their acid or base salts, organic or mineral, and / or their solvates such as hydrates.

Description

Title of the invention: Cosmetic or dermatological composition comprising a merocyanine and a thiopyridinone compound

[0001] The present invention relates to a cosmetic or dermatological composition comprising at least one aqueous phase, at least one merocyanin of formula (3) which will be defined in detail later and at least one compound of formula (I) or (!'), as described below, and / or their optical isomers, geometric isomers as well as their acid or base salts, organic or mineral, and / or their solvates such as hydrates. technical field

[0002] It is known that radiation with wavelengths between 280 nm and 400 nm allows the human epidermis to tan, and that radiation with wavelengths between 280 and 320 nm, known as UV-B rays, interferes with the development of a natural tan. Exposure is also likely to induce an alteration of the biomechanical properties of the epidermis, resulting in the appearance of wrinkles and leading to premature skin aging.

[0003] It is also known that UV-A rays with wavelengths between 320 and 400 nm penetrate the skin more deeply than UV-B rays. UV-A rays cause immediate and persistent tanning of the skin. Daily exposure to UVA rays, even for short periods, under normal conditions can lead to the degradation of collagen and elastin fibers, resulting in changes to the skin's microrelief, the appearance of wrinkles, and uneven pigmentation (brown spots, uneven skin tone).

[0004] Protection against UVA and UVB radiation is therefore necessary. An effective photoprotection product must protect against both UVA and UVB radiation.

[0005] Numerous photoprotective compositions have been proposed to date to counteract the effects induced by UVA and / or UVB radiation. They generally contain UV filters that function according to their own chemical nature and their own properties by absorption, reflection, or scattering of UV radiation, such as, for example, mixtures of liposoluble organic UV filters and / or water-soluble organic UV filters.

[0006] Numerous cosmetic compositions designed to limit skin darkening and improve skin tone and evenness have been proposed to date. It is well known in the field of sunscreens that such compositions can be obtained using UV filters, and in particular UVB filters. Some compositions may also contain UVA filters. This filtering system must cover UVB protection in order to limit and control the neosynthesis of melanin which promotes overall pigmentation, but must also cover UVA protection in order to limit and control the oxidation of already existing melanin which leads to the darkening of skin color.

[0007] However, it is extremely difficult to find a composition containing a particular combination of UV filters that would be specially adapted for the photoprotection of the skin and particularly for an improvement in the quality of the skin both in terms of color and its mechanical properties of elasticity.

[0008] Advantageously, this improvement is particularly sought on already pigmented skin in order not to increase either the pigment load in melanin or the structure of the melanin already present in the skin.

[0009] In fact, the majority of organic UV filters consist of aromatic compounds absorbing in the wavelength range between 280 and 370 nm. In addition to their ability to filter solar radiation, the desired photoprotective compounds must also exhibit good cosmetic properties, good solubility in common solvents, particularly in fatty substances such as oils or in water, as well as good photostability, either alone or in combination with other UV filters. They must also be colorless or at least have a color that is cosmetically acceptable to the consumer.

[0010] One of the main drawbacks known to date of these compositions is that these filtering systems have insufficient effectiveness against UV radiation and particularly against long UVA radiation with wavelengths beyond 370 nm in order to control photo-induced pigmentation and its evolution by a UV filtering system over the entire UV spectrum.

[0011] Among all the compounds that have been recommended for this purpose, a An interesting family of UV filters consisting of carbon-based merocyanine derivatives is described in US patent 4195999, application WO2004 / 006878, and document IP COM Journal 4 (4), 16 No. IPCOM000011179D published on 04 / 03 / 2004. These compounds exhibit very good filtration properties in long-wave UVA radiation but have only slightly satisfactory solubility in common solvents, both in aqueous and oily phases, and unsatisfactory photostability for some merocyanines.

[0012] In order to find other merocyanins with better solubility in common solvents and better photostability, application WO2013 / 011094 proposed merocyanins comprising polar groups consisting of hydroxyl and ether functions that show good filtration efficiency of long UVA rays. However, the solubility of these particular merocyanins is not While not entirely satisfactory, it often requires a tedious formulation process. Furthermore, the significant quantities of solvent needed to solubilize this type of merocyanine can lead to cosmetic issues such as a sticky and greasy feeling upon application.

[0013] There therefore remains a need to improve the solubility of these merocyanins in cosmetic compositions, in particular photo-protective formulations, especially in an aqueous phase, while obtaining good cosmetic properties.

[0014] Furthermore, a depigmenting or bleaching agent that is a thiopyridinone compound is known from patent applications WO2012 / 080075 and WO2017 / 102349. The thiopyridinone compound exhibits particularly effective depigmenting or bleaching properties by reducing melanin production.

[0015] The Applicant has surprisingly discovered that by using such a thiopyridinone compound, it is possible to substantially improve the solubility of the aforementioned merocyanins, particularly in an aqueous phase. This discovery forms the basis of the present invention.

[0016] Thus, in accordance with one of the objects of the present invention, a cosmetic or dermatological composition is now proposed comprising at least one merocyanin of formula (3) which will be defined in detail later and at least one compound of formula (I) or (I'), as described below, and / or their optical isomers, geometric isomers as well as their acid or base salts, organic or mineral, and / or their solvates such as hydrates.

[0017] Furthermore, there is also a need to improve the solubility of merocyanins in the presence of additional UV filters. Indeed, the addition of additional UV filters can destabilize compositions containing a merocyanin.

[0018] The present invention is specifically designed to meet these needs.

[0019] The Applicant has surprisingly discovered that by using a thiopyridinone compound, and / or an optical isomer, geometric isomer as well as an acid or base salt, organic or mineral, and / or a solvate such as a hydrate, it was possible to substantially improve the solubility of these merocyanins in an aqueous phase, even in the presence of additional UV filters.

[0020] The Applicant also discovered that the use of at least one thiopyridinone compound, and / or an optical isomer, geometric isomer as well as an acid or base salt, organic or mineral, and / or a solvate such as a hydrate made it possible to obtain good cosmeticity of the composition comprising the merocyanins, the latter being in particular non-greasy and non-sticky. Description of the invention

[0021] Thus, the present invention relates to a cosmetic or dermatological composition comprising: (a) at least one aqueous phase; (b) at least one merocyanin corresponding to the following formula (3), together with their isomeric geometric forms, in particular E / E or E / Z: in which: A is -O- or -NH; R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alcinyl group, a C3-C22 cycloalkyl group, or a C3-C22 cycloalkenyl group, said groups being able to be interrupted by one or more O groups; and (c) at least one compound selected from compounds of formula (I), tautomers of formula (!'), their salts, their solvates, such as their hydrates, their optical isomers, their racemates, and mixtures thereof: W 03 in which: - Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in C1-C10 or branched in C3-C10 optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and - R2 designates a radical chosen from a) a hydrogen atom, b) a linear saturated hydrocarbon group in C1-C12 or a branched hydrocarbon group in C3-C12 or a cyclic hydrocarbon group in C3-C8 optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyl groups and / or by one or more CrC8j alkoxy radicals and c) a C5-C12 aryl group, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in CrC8et - R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-Cio or branched in C3-Ci0.

[0022] This composition may optionally include at least one additional UV filter.

[0023] The present invention makes it possible to obtain purely aqueous cosmetic or dermatological compositions or in the form of emulsions, stable over time without any recrystallization being observed, having good cosmetic properties, in particular being non-greasy and non-sticky, providing filtration in the long UVA and an effect on pigmentation induced by radiation in the UV and visible.

[0024] The present invention also relates to a non-therapeutic cosmetic process for the care and / or makeup of a keratinous material comprising the application on the surface of said keratinous material of at least one composition according to the invention as defined above.

[0025] It also relates to a non-therapeutic cosmetic process for limiting skin darkening and / or improving the color and / or homogeneity of the complexion comprising the application on the surface of the keratinous material of at least one composition as defined above.

[0026] It also relates to a non-therapeutic cosmetic process for preventing and / or treating the signs of aging of a keratinous material comprising the application on the surface of the keratinous material of at least one composition as defined above.

[0027] The present invention also relates to the use of at least one thiopyridinone compound, and / or an optical isomer, geometric isomer as well as an acid or base salt, organic or mineral, and / or a solvate such as a hydrate to solubilize a merocyanin of formula (3) as defined below, in particular to solubilize these molecules in aqueous phase.

[0028] Other features, aspects and advantages of the invention will become apparent from the detailed description that follows.

[0029] The composition according to the invention is intended for topical application and therefore contains a physiologically acceptable medium. Hereinafter, "physiologically acceptable medium" means a medium compatible with keratinous materials.

[0030] In the context of the present invention, "keratinous material" shall include, in particular, the skin, scalp, keratinous fibers such as eyelashes, eyebrows, hair, and body hair, nails, mucous membranes such as lips, and more specifically the skin and mucous membranes (body, face, eye contour, eyelids, lips, preferably body, face and lips).

[0031] In what follows, and unless otherwise indicated, the bounds of a range of values ​​are included in that range, in particular in the expressions "between" and "ranging from ... to ...".

[0032] Furthermore, the expressions "at least one" and "at least" used in this description are respectively equivalent to the expressions "one or more" and "greater than or equal to".

[0033] By "prevent" or "prevention", according to the invention, means reducing the risk of occurrence or slowing down the occurrence of a given phenomenon, namely, according to the present invention, the signs of aging of a keratinous material. Detailed description of the invention Merocyanins

[0034] According to the present invention, a family of merocyanins corresponding to the following formula (3) and their isomeric geometric forms, in particular E / E- or E / Z-, will be used. in which: A is -O- or -NH; R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alcinyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups being able to be interrupted by one or more O's.

[0035] The merocyanine compounds of the invention can be in their isomeric geometric forms E / E-, E / Z-:

[0036] The compounds of formula (3) that are even more preferred are those where: A is -O- ; R is a Ci-C22 alkyl, which can be interrupted by one or more O's.

[0037] Among the compounds of formula (3), we will use in particular those chosen from the following group as well as their isomeric geometric forms, notably E / E-, E / Z-: 14 °^°x^ H Y Y Y ethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-l-ylid ene]ethanoate 15 1 H | H ] Y / N^^x^x Y Y Y (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methoxypropyl)amino ] cyclohex-2-en-1 -ylidene} ethanamide 25 x / 'X-x x^jX.xJx Y Y 2-ethoxyethyl (2Z)-cyano{ 3-[(3-methoxypropyl)amino]cyclohex-2-en-1 - ylidene} ethanoate 27 1 1 O O^O ^Y ] H 1 YNx^ / Y Y Y 2-methylpropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex- 2-en-1-ylidene] ethanoate 29 1 Ox^O^ / x„^x. / x I n Y x^o-V\ k^-N^x^x Y Y 2-butoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1 - ylidene} ethanoate 31 1 | H I k^N^ÿx-Axx Y Y 3-methoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1 -ylidene} ethanoate 37 1 o ] H 1 1 1 TT -n 3-ethoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene] ethanoate

[0038] According to a more particularly preferred embodiment of the invention, the compound 2-ethoxyethyl (2Z)-cyano{ 3-[(3-methoxypropyl)-amino]cyclohex-2-en-1-ylidene]ethanoate (25) will be used in its E / E and / or E / Z geometric configuration.

[0039] The E / Z form has the following structure:

[0040] The E / E form has the following structure:

[0041] As an example of compounds of formula (3), we can cite the raw material whose INCI name is METHOXYPROPYLAMINO CYCLOHEXENYLIDENEETHOXYETHYLCYANOACETATE.

[0042] The filtering merocyanins according to the invention can be present in the compositions according to the invention in a concentration ranging from 0.1% to 15% by weight, and preferably from 0.2% to 10% by weight and even better from 0.5% to 5% by weight relative to the total weight of the composition.

[0043] The compounds of formula (3), which form a carbocyclic ring containing 6 carbon atoms, can be prepared according to the protocols described in Pat. Appl. WO 2007 / 071582, in IP.com Journal (2009), 9(5A), 29-30 IPCOM000182396D under the heading “Process for producing 3-amino-2-cyclohexan-l-ylidene compounds” and in US-A-4,749,643 on col. 13, line 66 - col. 14, line 57 and the references cited therein.

[0044] In particular, compounds of formula (3), such as the compound 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)-amino]cyclohex-2-en-l-ylidene}ethanoate (25) may to be synthesized according to the synthesis scheme described in the publication by B. Winkler et al., Tetrahedron Letters, 55 (2014) 1749-1751, entitled “A cyclic merocyanine UV-A absorber: mechanism of formation and crystal structure”, and represented below, for compounds of formula (3):

[0045] And more specifically for compound 25 described in Table 1: Thiopyridinone compounds

[0046] The composition according to the present invention comprises at least one thiopyridinone compound. Two or more distinct thiopyridinone compounds, of formula (I) or (!'), may be used in combination. Thus, a single thiopyridinone compound of formula (I) or (!') or a combination of different thiopyridinone compounds of formula (I) or (!') may be used.

[0047] The thiopyridinone compound(s) are selected from the compounds of formula (I) below, the tautomers of formula (!') below, their salts, their solvates, such as their hydrates, their optical isomers, their racemates and their mixtures (0 © in which: Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-Cio or branched in C3-CiO optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and R2 denotes a radical chosen from a) a hydrogen atom, b) a linear saturated hydrocarbon group in Ci-Ci2 or branched in C3-Ci2 or cyclic in C3-C8, optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in CrC8, and c) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in CrC8, and R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-Cio or branched in C3-Ci0.

[0048] Hereinafter, within the meaning of the present invention and unless otherwise indicated: - a "saturated, linear in Ci-Ci2 or branched in C3-Ci2" hydrocarbon group is equivalent to a "linear (in C1-C12) or branched (in C3-Ci2) alkyl group" which corresponds to a saturated, linear in CrCi2 or branched in C3-Ci2 hydrocarbon group, preferably a linear in Ci-Cio or branched in C3-Ci0 hydrocarbon group, and more preferably a linear in Ci-C6 or branched in C3-C6 hydrocarbon group; preferably, the linear or branched groups may be chosen from among the methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl groups; More preferably, the saturated alkyl groups, linear or branched, can be chosen from the methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl and octyl groups, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl; - a saturated hydrocarbon group "cyclic in C3-C8" is a mono- or bicyclic cycloalkyl group containing 3 to 8 carbon atoms, and in particular is a monocyclic cycloalkyl group in C5 to C7 such as a cyclohexyl group, - an "alkoxy radical" is an alkyl-oxy radical for which the alkyl radical is a linear or branched hydrocarbon radical in CrCi6, and preferably a hydrocarbon radical in Ci-C8; - when the alkoxy group is optionally substituted, this implies that the alkyl group is optionally substituted as defined above; - an "aryl" group represents a carbon-based group, monocyclic or bicyclic, fused or not, comprising from 5 to 12 carbon atoms, preferably from 6 to 10 carbon atoms, and in which at least one ring is aromatic; preferably, the aryl radical is a phenyl, biphenyl, naphthyl group, more preferably a phenyl group; - the expression "at least one" is equivalent to the expression "one or more"; and - the term "inclusive" for a range of concentrations means that the limits of that range are included in the defined range.

[0049] The salts of compounds of formula (I), (I'), (II), or (II') as defined below include conventional non-toxic salts of said compounds, such as those formed from an organic or inorganic acid or an organic or inorganic base.

[0050] Examples of salts of compounds of formula (I), (I'), (II) or (II') include: Salts obtained by adding the compound of formula (I) or (II) to: a mineral base, such as sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and sodium, potassium, or calcium carbonate or hydrogen carbonate, for example; or An organic base such as a primary, secondary, or tertiary alkylamine, for example, triethylamine or butylamine. This primary, secondary, or tertiary alkylamine may contain one or more nitrogen and / or oxygen atoms and may thus include, for example, one or more alcohol groups. Examples include 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylaminopropanol, 2-amino-2-(hydroxymethyl)-1,3-propanediol, and 3-(dimethylamino)propylamine.

[0051] Other examples include amino acid salts, for instance lysine, arginine, guanidine, glutamic acid, and aspartic acid. Advantageously, the salts of compounds of formula (I) or (II) (when they include a carboxy group) can be selected from alkali or alkaline earth metal salts such as sodium, potassium, calcium, or magnesium salts and ammonium salts.

[0052] A "salt of an organic or inorganic acid" is more particularly chosen from salts chosen from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(O)2OH such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(O)2OH such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid; x) alkoxysulfinic acids: Alk-OS(O)OH such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid H3PO4; xiii) acetic acid CH3C(O)OH; xiv) triflic acid CF3SO3H; and xv) tetrafluoroboric acid HBF4.

[0053] Acceptable solvates of the compounds described in the specification include conventional solvates such as those formed during the preparation of said compounds due to the presence of solvents. Examples include solvates due to the presence of water or linear or branched alcohols, such as ethanol or isopropanol.

[0054] Optical isomers are, in particular, enantiomers and diastereomers.

[0055] Compound (!') is the tautomeric form of compound (I) when a tautomeric equilibrium exists according to the following scheme: (b (H

[0056] According to one embodiment of the present invention, Ri represents a hydrogen atom.

[0057] According to one embodiment of the present invention, Ri of formula (I) and (!') represents a linear (Ci-CiO) or branched (C3-CiO) alkyl group, in particular a linear (Ci-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably, ethyl. In particular, said alkyl group of Ri' is unsubstituted.

[0058] According to one embodiment of the present invention, R2 represents a hydrogen atom.

[0059] According to one embodiment of the present invention, R2 represents a linear (Ci-Ci0) or branched (C3-Ci0) alkyl group, in particular a linear (Cr C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group of R2 not being substituted.

[0060] According to one embodiment of the present invention, R2 of formula (I) and (!') represents a linear (Ci-Ci) or branched (C3-Ci) alkyl group, in particular a linear (Ci-C6) or branched (C3-Ci) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group being substituted by one or more groups selected from i), ii), iii) and iv) as defined above. Preferably, said alkyl group being substituted by one or two groups selected from i), ii) and iii), more preferably by one or two groups selected from i) and iii), better substituted by a group iii) as a carboxy.

[0061] Another variant for the radical R2 is that said alkyl group is substituted by a group iv) in particular substituted by a phenyl group.

[0062] According to another embodiment of the present invention, R2 represents a cycloalkyl group (in C3-C8), preferably a cycloalkyl group (in C5-C7) such as cyclohexyl.

[0063] According to another embodiment of the present invention, R2 represents an aryl group in C5-Ci2 optionally substituted by one or more hydroxyls and / or by one or more alkoxy radicals in Ci-C8, preferably a phenyl group in particular unsubstituted.

[0064] According to one embodiment, R3 represents a hydrogen atom.

[0065] According to another embodiment, R3 represents a saturated alkyl group, linear in C1-C10 or branched in C3-Ci0; in particular a linear (in Ci-C6) or branched (in C3-C6) alkyl group, preferably an alkyl group (in CrC4) such as the methyl group.

[0066] Preferably, the compounds of formula (I) and the tautomer (!') or their salts, their optical isomers, racemates, and / or solvates such as their hydrates and their derivatives, alone or in mixture, have the following meanings: Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-C6 or branched in C3-C6 optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, preferably optionally substituted by one or more i) groups; R2 denotes a radical chosen from a) a hydrogen atom; b) a linear saturated hydrocarbon group in C1-C10 or branched in C3-C10 or cyclic in C3-C8 such as in C5-C6 optionally substituted by one or more groups, which may be the same or different, selected from: i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a phenyl group optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in C1-C4 such as methoxy, preferably substituted by one or more groups selected from i) and iii), preferably iii) such as carboxy; and R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-C6 or branched in C3-C6.

[0067] Preferably, the compounds of formula (I) and the tautomer (!') or their salts, their optical isomers, racemates, and / or their solvates such as their hydrates, alone or in mixture, have the following meanings: Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in C1-C4 or branched in C3-C4 optionally substituted by one or more groups, which may be identical or different, chosen from i) -OR3>plus preferably unsubstituted; R2 denotes a radical chosen from a) a hydrogen atom; and b) a linear saturated hydrocarbon group in C1-C10 or a branched hydrocarbon group in C3-C10 or a cyclic hydrocarbon group in C3-C8 as in C5-C6, optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, iii) -C(O)-O-R3, iv) an aryl group in C5-C12, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in C1-C4; and R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in C1-C4 or branched in C3-C4 such as methyl or ethyl.

[0068] Preferably, the compounds of formula (I) and the tautomer (!') or their salts, their optical isomers, racemates, and / or solvates such as hydrates and their derivatives, alone or in mixture, have the following meanings: Ri is a hydrogen atom; and R2 denotes a radical chosen from a) a hydrogen atom, and b) a saturated hydrocarbon group, linear in C1-C5 or branched in C3-C5 or cyclic in C3-C8 such that C5-C6 may be identical or different, chosen from v) -C(O)-O-R3, preferably substituted by a group iii) -C(O)-O-R3; R2 is more preferably a saturated hydrocarbon group, linear in C1-C4 or branched in C3-C4 substituted by a group iii) -C(O)-OR3; and R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in C1-C4 or branched in C3-C4 such as methyl or ethyl.

[0069] According to another preferred embodiment, the compounds of formula (I) and the tautomer (!') are selected from the compounds of formula (II) below and also their tautomers of formula (II') below, their salts, their solvates and their optical isomers, and their racemates, alone or in mixture: OAM .X § y ) 1 X 'SH OY ô HY c (II) (il')

[0070] In formula (II) and (II'), Ri and R3 have the same meaning as Ri and R3 for the compounds of formula (I) and (I'), and X denotes an alkylene radical -(CH2)n- with n being an integer from 1 to 10 inclusive, preferably from 1 to 6, more preferably from 1 to 4, such that 1, preferably, R3 represents a hydrogen atom.

[0071] Among the compounds of formula (I), the following compounds are preferably used, and their tautomer (I') or their salts, their optical isomers, racemates, and / or solvates such as hydrates and their derivatives, alone or in mixture: No. Structure Chemical Name CAS No. 1 $ N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-75-5 2 Y ......SX \y N-methyl-2-thioxo-1,2-dihydroxydropyridine-3-carboxamide 91859-74-4 3 N-octyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-77-7 4 X 7 f'"' N-benzyl-2-thioxo-1,2-dihydroxydropyridine-3-carboxamide 91859-79-9 5 # xx ----k --VY \x. x^ N-phenyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 104857-16-1 6 ï; E H H N-cyclohexyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-78-8 7 h r ji L .-K N- [2- (4-méthoxyphény l)é thy 1] -2-thioxo-1,2-d ihydropyridine-3-carbo xamide 923682-88-6 8 X •m ^>LX .5^ ,.A, k if N-(2-méthylpropyl)-2-t hioxo-1,2-dihydropyrid ine- 3 -carboxamide 1100027-79 -9 9 •••‘ "■•\-y''" XV“"’ X^-'‘ :• H ■■W'’'' ' ■ x 's N-pentyl-2-thioxo-1,2-dihydropyridine-3-carb oxamide 330667-57-7 10 ■ yly N-nonyl-2-thioxo-1,2-d ihydropyridine-3-carbo xamide 1031149-44 -6 11 Y=xx \ / / \ / / ( y N-(2-hydroxyéthyl)-2-t hioxo-1,2-dihydropyrid ine- 3 -carboxamide 12 □ is | X<*S '''CHs N,N-diethyl 2-mercapt onicotinamide 13 YZ Y — ■ : \ x—œ YY N-ethyl-N-(2-hydroxyethyl)-2-thioxo-1,2-dihydroxydropyridine-3-carbamide 14 : ,L\.^ .-^ K .' . -¼ ' ' ■ N-(2,3-dihydroxypropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 15 0 r'' N-(1,3-dihydroxypropan-2-yl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 16 a CHj ''W'" "^s \ H / N- [(2-thioxo-1,2-dihydropyridine-3-yl)carbonyl]ethyl alaninate 17 S-^ 1 :i ' N- [(2-thioxo-1,2-dihydropyridine-3-yl)carbonyl]ethyl phenyl alaninate 18 'N" N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 19 k N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 20 IL OH CX " f N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine 21 «.j! ffYVY CK OH H N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl] glycine 22 .^¾. ^yr* ^yr x N,N-bis(2-hydroxyethyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 23 O. a. Jl '<-'1 N-(3-methoxypropyl)-2 -thioxo-1,2-dihydropyridine- 3 -carboxamide 24 $ H N-butyl-2-thioxo-1,2-d ihydropyridine-3-carbo xamide

[0072] Among these compounds, the following compounds are particularly preferred: Structure No. Chemical Name CAS No. 1 .jX x' pf Y * Ys H N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-75-5 2 .............. N-methyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-74-4 4 N-benzyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-79-9 6 ,.--s .-YY -XJX sy 'N ■■ h MH N-cyclohexyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-78-8 7 Ç- zX" XH- zx P '1 H N- [2- (4-methoxyphenyl)e thy 1] -2-thioxo-1,2-d ihydropyridine-3-carbo xamide 923682-88-6 9 >x, Y^::- N-pentyl-2-thioxo-1,2-dihydropyridine-3-carb oxamide 330667-57-7 11 Ü 7 À YY 'v5 fi N-(2-hydroxyethyl)-2-t hioxo-1,2-dihydropyrid ine-3-carboxamide 12 ( T T.”" iÀ N,N-diethyl 2-mercapt onicotinamide 14 J*- z'0H N-(2,3-dihydroxypropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 15 _.Zx. M Â .OH N-(1,3-dihydroxypropan-2-yl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 16 \ M î' h3c N- [(2-thioxo-1,2-dihydropyridine-3-yl)carbonyl]ethyl alaninate 17 v- A, N- [(2-thioxo-1,2-dihydropyridine-3-yl)carbonyl]ethyl phenyl alaninate 18 p T zx'5>'' ""'N - ethyl N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate 19 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 20 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine 21 CH. GH H N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine

[0073] More preferably, among these compounds, the following compounds are particularly preferred: Structure No. Chemical Name CAS No. 1 H N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-75-5 9 C: x-xyy>'' '■fi''*” $ H N-pentyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 330667-57-7 16 .XY * jj ? Y"" Y \ H / N- [(2-thioxo-1,2-dihydropyridine-3-yl)carbonyl ]ethyl alaninate 18 N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 19 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 20 _ 1 [Q r ï AC N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine 21 / Vo / " \ Y 'O N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl] glycine Even more preferably, among these compounds, the following compounds are more

[0074] particularly preferred: No. Structure Chemical Name CAS No. 18 . I ,o ( Y" YTH OY N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 19 G t J - ''■'N'"' H N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl ]ethyl glycinate

[0075] In a most preferred embodiment, the compound according to the present invention is as follows: 20 THERE s >5 N-[(2-thioxo-1,2-dihyd ropyridin-3-yl)carbony l]glycine

[0076] All the above compounds can be obtained by a chemical process known to those skilled in the art, from commercially available reagents.

[0077] The thiopyridinone compound (1) can be prepared in accordance with the process described, for example, in document EP-A-3390363 or WO 2017 / 102349, which is incorporated by reference.

[0078] The compound thiopyridinone (1) can be an active ingredient or active compound in cosmetic or dermatological products. The term "active ingredient" or "active compound" used here refers to an ingredient or compound that has an active cosmetic or dermatological property, such as antioxidant, bleaching, UV-filtering, and antibacterial effects. The compound thiopyridinone (1) used in the present invention can function as a depigmenting, bleaching, or bleaching agent, and thus the composition according to the present invention can be used as a bleaching product or as a cosmetic composition for bleaching keratinous material.

[0079] The compound thiopyridinone (1) can be used as an agent for depigmenting, bleaching or whitening the skin, body hair, eyelashes or hair, and also the lips and / or nails, and preferably the skin, in particular for removing pigmentation spots or age spots, and / or as an anti-tanning agent.

[0080] The amount of the thiopyridinone compound(s) (1) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.05% by weight. weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.

[0081] Furthermore, the quantity of the thiopyridinone compound(s) (1) in the composition according to the present invention may be 10% by weight or less, preferably 5% by weight or less, and more preferably 3% by weight or less, relative to the total weight of the composition.

[0082] The quantity of the thiopyridinone compound(s) (1) in the composition according to the present invention can range from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight, more preferably from 0.1% to 3% by weight, relative to the total weight of the composition. Additional UV filters

[0083] The composition according to the invention may further include at least one additional UV filter.

[0084] The additional UV filter(s) may in particular be chosen from among organic UV filters, and in particular hydrophilic organic UV filters, such as water-soluble organic UV filters and water-dispersible organic UV filters, and lipophilic organic UV filters.

[0085] By "water-soluble organic UV filter" is meant any organic UV filter capable of being totally dissolved in molecular form in a liquid aqueous phase.

[0086] By "hydrodispersible organic UV filter" is meant any organic UV filter capable of forming in a liquid aqueous phase a homogeneous suspension of particles with a volume average size of less than 100 microns. The volume average size is determined by laser diffraction particle size analysis.

[0087] By "lipophilic organic UV filter" is meant any organic filter capable of being completely dissolved in molecular form in a liquid oil phase or of being solubilized in colloidal form (for example in micellar form) in a liquid oil phase.

[0088] By "organic UVA filter" is meant any organic chemical molecule capable of absorbing at least UVA radiation in the wavelength range between 320 and 400 nm; said molecule also being able to absorb UVB radiation in the wavelength range between 280 and 320 nm.

[0089] By "organic UVB filter" is meant any organic chemical molecule capable of absorbing mainly UVB radiation in the range of wavelengths between 280 and 320 nm. Water-soluble organic UV filters

[0090] The composition according to the invention may include at least one water-soluble organic UV filter.

[0091] Among the water-soluble organic filters capable of absorbing UVA, we can mention: - the compound with INCI name Terephthalylidene Dicamphor Sulfonic Acid manufactured under the name "MEXORYL SX" by NOVEAL; - bis-benzoazolyl derivatives as described in EP 669 323 and US 2,463,264, and more particularly the compound with the INCI name Disodium Phenyl Dibenzimidazole Tetrasulfonate sold under the trade name "NEO HELIOPAN AP" by SYMRISE.

[0092] The water-soluble organic filter may also be a mixed water-soluble filter capable of absorbing UVA and UVB. Preferably, such a mixed filter is a benzophenone derivative comprising at least one sulfonic acid radical, such as, in particular: Benzophenone-4 sold under the trade name "UVINUL® MS40" by BASF, Benzophenone-5, and Benzophenone-9.

[0093] According to a particular embodiment of the invention, the water-soluble organic filter(s) capable of absorbing UVA are chosen from Terephthalylidene Dicamphor Sulfonic Acid, bis-benzoazolyl derivatives, in particular Disodium Phenyl Dibenzimidazole Tetrasulfonate, Benzophenone-4, Benzophenone-5, Benzophenone-9 and mixtures thereof.

[0094] Preferably, the water-soluble organic filter(s) capable of absorbing UVA are chosen from Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetrasulfonate, Benzophenone-4, Benzophenone-5, Benzophenone-9 and mixtures thereof.

[0095] Even more preferably, the water-soluble organic filter(s) capable of absorbing UVA are chosen from Terephthalylidene Dicamphor Sulfonic Acid, bis-benzoazolyl derivatives, in particular Disodium Phenyl Dibenzimidazole Tetrasulfonate, and mixtures thereof.

[0096] Preferably, the water-soluble organic filter(s) capable of absorbing UVA is chosen from Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetrasulfonate, and mixtures thereof.

[0097] According to a first preferred embodiment, the water-soluble organic filter capable of absorbing UVA is Terephthalylidene Dicamphor Sulfonic Acid (also called Ecamsule).

[0098] According to a second preferred embodiment, the water-soluble organic filter capable of absorbing UVA is Disodium Phenyl Dibenzimidazole Tetrasulfonate (also called Bisdisulizole Disodium).

[0099] The water-soluble organic UVB filter(s) usable according to the present invention may be chosen from water-soluble cinnamic derivatives such as ferulic acid or 3-methoxy-4-hydroxycinnamic acid; water-soluble benzylidene camphor compounds; water-soluble phenylbenzimidazole compounds; water-soluble p-aminobenzoic compounds (PABA), Glyceryl PABA or PEG-25 PABA sold under the name "UVINUL® P25" by BASF; water-soluble salicylic compounds, Benzylidene Camphor Sulfonic Acid manufactured under the name "MEXORYL SL" by NOVEAL, Camphor Benzalkonium Methosulfate manufactured under the name "MEXORYL SO" by NOVEAL, and mixtures thereof.

[0100] Preferred examples of water-soluble organic UVB filters include phenylbenzimidazole compounds, such as 2-phenyl-1H-benzimidazole-5-sulfonic acid (INCI name: phenylbenzimidazole sulfonic acid) sold in particular under the trade name "EUSOLEX 232®" by MERCK.

[0101] According to a preferred embodiment, the water-soluble organic filter capable of absorbing UVB is Phenylbenzimidazole Sulfonic Acid (also called Ensulizole). Water-dispersible organic UV filters

[0102] The hydrodispersible organic UV filter(s) can be chosen from the following compounds.

[0103] Methylene bis-(hydroxyphenyl benzotriazole) compounds:

[0104] Methylene bis-Benzotriazolyl Tetramethylbutylphenol in the form of an aqueous dispersion of micronized particles having a volume average particle size ranging from 0.01 to 5 µm, and more preferably from 0.01 to 2 µm, and more particularly from 0.020 to 2 µm, with at least one alkylpolyglycoside surfactant of the structure CnH2n+iO(C6HiO5)xH in which n is an integer from 8 to 16 and x is the average degree of polymerization of the unit (C6HiO5) and ranges from 1.4 to 1.6 such as the aqueous dispersions described in patent GB-A-2 303 549, in particular the product sold under the trade name "TINOSORB® M" by BASF, or in the form of an aqueous dispersion of micronized particles having a volume average particle size ranging from 0.02 to 2 qm, and more preferably from 0.01 to 1.5 qm, and more particularly from 0.02 to 1 qm,in the presence of at least one mono-(C8-C2o)alkyl-ester of polyglycerol having a degree of glycerol polymerization of at least 5 such as the aqueous dispersions described in application WO2009 / 063392, in particular the product marketed under the name Tinosorb WPGL by BASF, Triazine Compounds#: ,

[0105] - 3,3'-(l,4-Phenylene)bis(5,6-diphenyl-l,2,4-triazine), INCI name Phenylene Bis-Diphenyl triazine, notably marketed under the name Triasorb by Pierre Fabre; - Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine in its water-dispersible form, INCI name Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine (and) Acrylates / C12-22 Alkyl Methacrylate Copolymer, under the trade name TINOSORB® S LiteAqua by BASF, - symmetric triazine filters substituted with naphthalenyl groups or polyphenyl groups used in micronized form (average particle size of 0.02 to 3 pm) which can be obtained for example by the micronization process described in applications GB-A-2 303 549 and EP-A-893119, and in particular in aqueous dispersion form, in particular 2,4,6-tris(bi-phenyl)-triazine and 2,4,6-tris(ter-phenyl)-triazine marketed under the name TINOSORB® A2B by BASF and which is covered in patent applications WO06 / 035000, WO06 / 034982, WO06 / 034991, WO06 / 035007, WO2006 / 034992, WO2006 / 034985.

[0106] Among the water-dispersible organic UV filters, the following filters may also be mentioned: Benzophenone compounds#:

[0107] 1,1 '-(1,4-piperazinediyl)bis [1 - [2- [4-(diethylamino)-2-hydroxybenzoyl]phenyl] - Methanone (CAS 919803-06-8) as described in application WO2007 / 071584; this compound being advantageously used in micronized form (average volume size of 0.02 to 2 µm) which can be obtained, for example, by the micronization process described in applications GB-A-2 303 549 and EP-A-893119 and in particular in aqueous dispersion form, Benzoxazole compounds#:

[0108] 2-[4-(l,3-benzoxazol-2-yl)phenyl]-l,3-benzoxazole, of cas number 904-39-2. Lipophilic organic UV filters

[0109] The lipophilic organic filter(s) may be selected from cinnamic compounds; anthranilate compounds; salicylic compounds; dibenzoylmethane compounds; benzylidene camphor compounds; benzophenone compounds; [3,[3-diphenylacrylate] compounds; triazine compounds; benzotriazole compounds; benzalmalonate compounds, in particular those cited in US patent 5624663; benzimidazole derivatives; imidazoline compounds; bis-benzoazolyl compounds as described in patents EP669323 and US 2,463,264; methylene bis-(hydroxyphenyl benzotriazole) compounds as described in applications US 5,237,071, US 5,166,355, GB2303549, DE 197 26 184 and EP893119; benzoxazole compounds as described in patent applications EP0832642, EP1027883, EP1300137 and DE10162844; filter polymers and filter silicones such as those described in particular in application WO-93 / 04665; α-alkylstyrene derived dimers such as those described in patent application DE19855649; 4,4-diarylbutadiene compounds such as those described in applications EP0967200, DE19746654, DE19755649, EP-A-1008586, EPI 133980 and EP133981 and mixtures thereof.

[0110] Preferably, the lipophilic organic filter(s) are chosen from salicylic compounds, dibenzoylmethane compounds, benzylidene camphor compounds; benzophenone compounds; triazine compounds; benzotriazole compounds; and mixtures thereof.

[0111] Examples of lipophilic organic photoprotective agents include those designated below by their INCI name and / or chemical name. Cinnamic compounds:

[0112] Ethylhexyl Methoxycinnamate sold in particular under the trade name PARSOL® MCX by the company DSM Nutritional Products; Isoamyl p-Methoxycinnamate sold under the trade name NEO HELIOPAN E 1000 ® by the company Symrise, Dibenzoylmethane compounds:

[0113] Butyl Methoxydibenzoylmethane (or avobenzone) sold notably under the trade name PARSOL® 1789 by DSM Nutritional Products, Salicylic compounds#:

[0114] Homosalate sold under the name "Parsol® HMS" by DSM Nutritional Products, Ethylhexyl Salicylate sold under the name "NEO HELIOPAN® OS" by Symrise, P,P-diphenylacrylate compounds#:

[0115] Octocrylene sold in particular under the trade name “UVINUL® N 539 T” by BASF, Benzophenone compounds#:

[0116] Benzophenone-3 or Oxybenzone, sold under the trade name "UVINUL® M 40" by BASF, Diethylamino hydroxybenzoyl hexyl benzoate sold under the trade name "UVINUL® A Plus" or in a mixture with ethylhexyl methoxycinnamate under the trade name "UVINUL® A Plus B" by BASF, Benzylidene camphor compounds#:

[0117] 4-Methylbenzylidene camphor sold under the name “EUSOLEX® 6300” by the company MERCK, Phenyl benzotriazole compounds#:

[0118] Drometrizole Trisiloxane manufactured under the name “MEXORYL® XL” by the company NOVEAL,

[0119] Methylene bis-(hydroxyphenyl benzotriazole) compounds:

[0120] Methylene bis-Benzotriazolyl Tetramethylbutylphenol, particularly in solid form such as the product sold under the trade name "MIXXIM BB / 100 ®" by FAIRMOUNT CHEMICAL, Triazine compounds#:

[0121] - Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine sold under the trade name “TINOSORB® S” by the company BASF, - Ethylhexyl Triazone, sold notably under the trade name "UVINUL® T 150" by BASF, - Diethylhexyl Butamido Triazone sold under the trade name "UVASORB® HEB" by the company 3V SIGMA, - symmetrical triazine filters substituted by naphthalenyl groups or polyphenyl groups described in US patent 6,225,467, application WO2004 / 085412 (see compounds 6 and 9) or the document "Symetrical Triazine Derivatives" IP.COM IPCOM000031257 Journal, INC WEST HENRIETTA, NY, US (September 20, 2004), Anthranilic compounds#:

[0122] Menthyl anthranilate sold under the trade name "NEO HELIOPAN® MA" by the company Symrise, Benzalmalonate compounds#:

[0123] Polyorganosiloxane with benzalmalonate functions such as Polysilicone-15 sold under the trade name “PARSOL SLX ®” by DSM NUTRITIONAL PRODUCTS.

[0124] According to a particular embodiment of the invention, the additional UV filter(s) are chosen from among the organic UV filters.

[0125] According to a first preferred embodiment of the invention, the organic UV filter(s) are chosen from among hydrophilic organic UV filters such as water-soluble organic UV filters and water-dispersible organic UV filters, preferably water-soluble organic UV filters.

[0126] According to a second preferred embodiment of the invention, the organic UV filter(s) are selected from lipophilic organic UV filters, preferably selected from Diethylamino hydroxybenzoyl hexyl benzoate (in particular sold under the trade name "UVINUL® A Plus") or in a mixture with ethylhexyl methoxycinnamate under the trade name "UVINUL® A Plus B" by the company BASF), Drometrizole Trisiloxane (notably manufactured under the name "MEXORYL® XL" by NOVEAL), Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine (notably sold under the trade name "TINOSORB® S" by BASF), Ethylhexyl Triazone (notably sold under the trade name "UVINUL® T 150" by BASF) and BUTYL METHOXYDIBENZOYLME THANE (notably sold under the trade name "PARSOL 1789 ®" by DSM NUTRITIONAL PRODUCTS).

[0127] When present in the composition according to the invention, the additional UV filter(s) may be present in an amount between 0.2% and 30% by weight, preferably between 0.5% and 25% by weight, preferably between 1% and 20% by weight, and even more preferably between 1.5% and 18% by weight relative to the total weight of the composition.

[0128] According to another embodiment of the invention, the additional UV filter(s) are present in an amount of less than 15% by weight, preferably less than 10% by weight, even more preferably less than 5% by weight, better less than 3% by weight, and even better less than 1% by weight relative to the total weight of composition. Aqueous phase

[0129] The composition according to the invention comprises at least one aqueous phase.

[0130] According to a particular embodiment, the composition according to the invention comprises at least one aqueous phase comprising at least water.

[0131] The aqueous phase may also comprise at least one other organic solvent soluble in water at 25 °C, chosen for example from: - C1-C4 monoalkanols. A "C1-C4 monoalkanol" is defined as any saturated, linear or branched alkane compound having from 1 to 4 carbon atoms and a single hydroxyl (OH) group. The C1-C4 monoalkanol(s) present in the compositions of the invention may be selected from methanol, ethanol, propanol, isopropanol, butanol, or mixtures thereof. Ethanol is particularly preferred; - polyols having in particular from 2 to 20 carbon atoms, preferably from 2 to 6 carbon atoms, such as glycerol, diglycerol, propylene glycol, isoprene glycol, dipropylene glycol, butylene glycol, hexylene glycol, 1,2-propanediol, 1,3-propanediol, pentylene glycol, caprylyl glycol, simple sugars, water-soluble polyalkylene glycols; and - their mixtures.

[0132] The monoalkanol(s) may be present at concentrations ranging from 0.2 to 90% by weight, more preferably from 0.5 to 50% by weight, and preferably from 1% to 10% by weight relative to the total weight of the composition.

[0133] According to a particular embodiment, the composition according to the invention comprises at least one polyol, in particular as described above. The presence of at least one polyol notably improves cosmetic properties, such as smoothness upon application, and reduces stickiness. Preferably, it comprises at least 0.5% by weight of polyols relative to the total weight of the composition, preferably at least 1% by weight of polyols relative to the total weight of the composition, preferably at least 3% by weight of polyols relative to the total weight of the composition, preferably at least 5% by weight of polyols relative to the total weight of the composition, preferably from 10% to 50% by weight, preferably from 15% to 40% by weight, preferably from 18% to 35% by weight, and even more preferably from 20% to 30% by weight.

[0134] Preferably, the composition according to the invention comprises a polyol, preferably glycerin, butylene glycol, propylene glycol, 1,2-propanediol, caprylyl glycol, pentylene glycol or dipropylene glycol and mixtures thereof.

[0135] According to a particular embodiment, the cosmetic composition according to the invention may comprise an acid and / or a base.

[0136] Examples of acidifying agents include mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, and sulfonic acids.

[0137] Examples of alkalizing agents include ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, sodium or potassium hydroxides.

[0138] Preferably, the cosmetic composition comprises one or more alkalizing agents selected from alkanolamines, in particular triethanolamine, and sodium hydroxide.

[0139] According to a particular embodiment, the composition according to the invention has a pH between 4 and 10, preferably between 5 and 8.5, and preferably between 5.5 and 8.

[0140] The pH measurement of the composition according to the invention can be carried out using a Mettler Toledo MPC227, SevenEasy pH or SevenGo SG2 pH meter, at room temperature (25 °C) and atmospheric pressure.

[0141] According to a particular embodiment of the invention, the overall aqueous phase, including all hydrophilic substances of the composition capable of being solubilized in this same phase, including hydrophilic filters, the or the merocyanines and the thiopyridinone compound(s) as defined above, represent from 5% to 100% by weight, and preferably from 30% to 100% by weight relative to the total weight of the composition.

[0142] The composition preferably comprises at least 5% by weight of water relative to the total weight of the composition, preferably from 10% to 99% by weight, even more preferably from 20% to 90% by weight, better from 30% to 80% by weight, and even better from 40% to 70% by weight relative to the total weight of the composition. Fat phase

[0143] According to a particular embodiment, the composition according to the invention comprises at least one fatty phase.

[0144] The oil phase may consist of any oily substances commonly used in cosmetics or dermatology. It may include at least one oil. The oil phase also includes the lipophilic filter(s) present in the composition.

[0145] The term "oil" refers to any fatty substance in liquid form at ambient temperature (20-25 °C) and atmospheric pressure (760 mm Hg). These oils may be volatile or non-volatile.

[0146] For the purposes of this invention, "volatile oil" means an oil capable of evaporating upon contact with the skin or keratin fiber in less than one hour, at ambient temperature and atmospheric pressure. The volatile oil(s) of the invention are volatile cosmetic oils, liquid at ambient temperature, having a non-zero vapor pressure at ambient temperature and atmospheric pressure, ranging in particular from 0.13 Pa to 40,000 Pa (103 to 300 mm Hg), in particular from 1.3 Pa to 13,000 Pa (0.01 to 100 mm Hg), and more particularly from 1.3 Pa to 1300 Pa (0.01 to 10 mm Hg).

[0147] By "non-volatile oil" is meant an oil remaining on the skin or keratin fiber at room temperature and atmospheric pressure for at least several hours and having in particular a vapor pressure of less than 103 mm Hg (0.13 Pa).

[0148] For the purposes of this invention, "hydrocarbon oil" means any oil consisting mainly of carbon and hydrogen atoms, and optionally one or more heteroatoms, in particular nitrogen and oxygen. Thus, these oils may notably contain one or more ester, ether, fluorine, carboxylic acid and / or alcohol groups.

[0149] The term “siliconized oil” means an oil comprising at least one silicon atom, and in particular at least one Si-O group.

[0150] Examples of non-volatile hydrocarbon oils that can be used according to the invention include: (i) vegetable hydrocarbon oils such as glyceride triesters, which are generally triesters of fatty acids and glycerol, the fatty acids of which may have chain lengths ranging from C4 to C24, the latter being linear or branched, saturated or unsaturated; these oils include wheat germ, sunflower, grape seed, sesame, maize, apricot, castor, shea, avocado, olive, soybean, sweet almond, palm, rapeseed, cottonseed, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, sesame, squash, rapeseed, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower, and rosehip oils; or even the triglycerides of caprylic / capric acids such as those sold by the company Stéarineries Dubois or those sold under the names Miglyol 810®, 812® and 818® by the company Dynamit Nobel; (ii) synthetic ethers having 10 to 40 carbon atoms; (iii) linear or branched hydrocarbons, of mineral or synthetic origin such as petroleum jelly, polydecenes, hydrogenated polyisobutene such as paream, squalane, and mixtures thereof; (iv) synthetic esters such as oils of the formula RCOOR' in which R represents the remainder of a linear or branched fatty acid comprising from 1 to 40 carbon atoms and R' represents a hydrocarbon chain, particularly a branched one, containing from 1 to 40 carbon atoms, provided that R + R' is >10, such as, for example, Purcellin oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, C12-C15 alcohol benzoates such as the product sold under the trade name "Finsolv TN®" or "Witconol TN®" by WITCO or "TEGOSOFT TN®" by EVONIK GOLDSCHMIDT, 2-ethylphenyl benzoate such as the commercial product sold under the name "X-TEND 226®" by ISP, isopropyl lanolate, hexyl laurate, diisopropyl adipate, isononyl isononanoate, oleyl erucate, 2-ethylhexyl palmitate, isostearyl isostearate,diisopropyl sebacate such as the product sold under the name "Dub Dis" by the company Stearinerie Dubois; octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate; hydroxylated esters such as isostearyl lactate, diisostearyl malate; and esters of pentaerythritol; citrates or tartrates such as linear C12-C13 dialkyl tartrates such as those sold under the name COSMACOL ETI® by the company ENICHEM AUGUSTA INDUSTRIALE, as well as linear C14-C15 dialkyl tartrates such as those sold under the name COSMACOL ETL® by the same company; acetates; , (v) fatty alcohols that are liquid at room temperature with a branched and / or unsaturated carbon chain having 12 to 26 carbon atoms such as octyl dodecanol, isostearyl alcohol, oleic alcohol, 2-hexyldecanol, 2-butyloctanol, 2-undecylpentadecanol; (vi) higher C12-C22 fatty acids, such as oleic acid, linoleic acid, linolenic acid; (vii) carbonates such as dicaprylyl carbonate such as the product sold under the name “Cetiol CC®” by the company Cognis; and their mixtures.

[0151] Among the non-volatile hydrocarbon oils usable according to the invention, glyceride triesters, and in particular caprylic / capric acid triglycerides, synthetic esters, and in particular diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate, dicaprylyl carbonate, isononyl isononanoate, oleyl erucate, C12-C15 alcohol benzoate, 2-ethylphenyl benzoate, and fatty alcohols, in particular octyldodecanol, are preferred. Preferably, the non-volatile hydrocarbon oils are chosen from diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate, and dicaprylyl carbonate.

[0152] Examples of usable volatile hydrocarbon oils according to the invention include hydrocarbon oils having 8 to 16 carbon atoms, and in particular C8-C16 branched alkanes such as C8-C16 petroleum-derived isoalkanes (also called isoparaffins) such as isododecane (also called 2,2,4,4,6-pentamethylheptane), isodecane, isohexadecane, oils sold under the trade names Isopars or Permetyls, C8-C16 branched esters, isohexyl neopentanoate, and mixtures thereof.

[0153] Also citeable are the alkanes described in Cognis patent applications WO 2007 / 068371 and WO 2008 / 155059 (mixtures of distinct alkanes differing by at least one carbon atom). These alkanes are obtained from fatty alcohols, themselves obtained from coconut or palm oil. Examples include the mixtures of n-undecane (Cl 1) and n-tridecane (Cl 3) obtained in Examples 1 and 2 of Cognis application WO 2008 / 155059. Also citeable are n-dodecane (C12) and n-tetradecane (C14) sold by Sasol under the references PARAFOL 12-97 and PARAFOL 14-97®, respectively, as well as mixtures thereof.

[0154] Other volatile hydrocarbon oils, such as petroleum distillates, particularly those sold under the name Shell Soit® by the Shell company, can also be used. In one embodiment, the volatile solvent is selected from volatile hydrocarbon oils having 8 to 16 carbon atoms and mixtures thereof.

[0155] Non-volatile silicone oils may be selected in particular from non-volatile polydimethylsiloxanes (PDMS), polydimethylsiloxanes comprising alkyl or alkoxy groups, during and / or at the end of the silicone chain, groups each having from 2 to 24 carbon atoms, phenyl silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, 2-phenylethyl trimethylsiloxysilicates.

[0156] Examples of volatile silicone oils include, for instance, volatile linear or cyclic silicone oils, particularly those with a viscosity < 8 centistokes (8 x 10⁶ m² / s), and having, in particular, 2 to 7 silicon atoms, these silicones possibly comprising alkyl or alkoxy groups having 1 to 10 carbon atoms. Examples of volatile silicone oils usable in the invention include, in particular, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof.

[0157] We can also mention volatile linear alkyltrisiloxane oils such as: 3-butyl 1,1,1,3,5,5,5-heptamethyl trisiloxane, 3-propyl 1,1,1,3,5,5,5-heptamethyl trisiloxane, and 3-ethyl 1,1,1,3,5,5,5-heptamethyl trisiloxane.

[0158] Fluorinated volatile oils, such as nonafluoromethoxybutane, decafluoropentane, tetradecafluorohexane, dodecafluoropentane and mixtures thereof, may also be used.

[0159] The oily phase according to the invention may further comprise, mixed with or solubilized in the oil, other fatty substances.

[0160] Another fatty substance that may be present in the oily phase may be, for example: - a fatty acid chosen from among fatty acids having 8 to 30 carbon atoms different from fatty chain amino acids as defined above, such as stearic acid, lauric acid, palmitic acid and oleic acid; - a gum chosen from among the silicone gums (dimethiconol), - a paste-like compound, such as polymeric or non-polymer silicone compounds, esters of an oligomeric glycerol, arachidyl propionate, fatty acid triglycerides and their derivatives, - and their mixtures.

[0161] According to a particular embodiment of the invention, the overall oily phase, including all the lipophilic substances of the composition capable of being solubilized in this same phase, including the lipophilic filters, represents from 0% to 90% by weight, and preferably from 0% to 70% by weight relative to the total weight of the composition. Active cosmetic ingredients

[0162] The composition of the present invention may include at least one cosmetic active ingredient.

[0163] Examples of cosmetic actives include moisturizing agents; natural extracts; vitamins and their derivatives; alpha-hydroxy acids; retinoids; extracts of algae, fungi, plants, yeasts and bacteria; enzymes; tightening agents; agents acting on microcirculation, and mixtures thereof.

[0164] It is easy for a person skilled in the art to adjust the quantity of cosmetic active ingredient according to the end use of the composition according to the present invention. Additional adjuvants or additives

[0165] The composition of the present invention may also include conventional cosmetic adjuvants or additives, for example perfumes, chelating agents, preservatives and bactericides, additional thickeners, pH regulators, additional fillers, and mixtures thereof.

[0166] A person skilled in the art can select the quantity of additional adjuvants or additives so as not to impair the final use of the composition according to the present invention. Pharmaceutical forms

[0167] According to a particular embodiment, the compositions according to the invention have a viscosity of at least 0.10 Pa.s, measured at 25 °C and under atmospheric pressure with a Lamy Rheology Rhéomat RM 100® viscometer after 10 minutes of measurement. Preferably, it is between 0.10 and 20 Pa.s, more preferably between 0.10 and 10 Pa.s, and better still between 0.10 and 5 Pa.s.

[0168] Such viscosity typically allows compositions to have a gel-like texture.

[0169] The compositions according to the invention can be prepared according to techniques well known to those skilled in the art.

[0170] The compositions according to the invention may be in aqueous form, for example in the form of an aqueous gel or hydroalcoholic composition, but also in the form of an emulsion, in particular an oil-in-water or water-in-oil emulsion, or a biphasic.

[0171] According to a particular embodiment, the composition of the invention does not comprise an oily phase. Preferably, the compositions according to the invention are oil-free. For the purposes of the invention, the term "oil-free" refers to a composition comprising a single liquid phase that is an aqueous phase (a liquid phase comprising water). The term "oil" does not cover, for example, the water-soluble active ingredients, water-soluble or water-dispersible UV filters and water-soluble glycols.

[0172] According to another particular embodiment, the composition according to the invention is in the form of an emulsion. When the composition according to the invention is in the form of an oil-in-water emulsion, it comprises an oily phase dispersed in an aqueous phase. When the composition according to the invention is in the form of a water-in-oil emulsion, it comprises an aqueous phase dispersed in an oily phase.

[0173] In the case of compositions in the form of oil-in-water or water-in-oil emulsions, the emulsification processes that can be used are of the blade or propeller type, rotor-stator and HHP.

[0174] It is also possible, by HHP (between 50 and 800 bars), to obtain stable dispersions with droplet sizes down to 100 nm.

[0175] Emulsions may generally contain at least one emulsifier selected from amphoteric, anionic, cationic, or nonionic emulsifiers, used alone or in mixtures. The emulsifiers are chosen appropriately according to the emulsion to be obtained (W / O or W / O).

[0176] Examples of non-ionic W / O emulsifying surfactants include alkyl esters or ethers of sorbitan, glycerol, polyol, glycerol or sugars; silicone surfactants such as dimethicone copolyols like the mixture of cyclomethicone and dimethicone copolyol sold under the name "DC 5225 C®" by Dow Corning, and alkyl-dimethicone copolyols such as Laurylmethicone copolyol sold under the name "Dow Corning 5200 Formulation Aid" by Dow Corning; Cetyl dimethicone copolyol, such as the product sold under the name Abil EM 90R® by Goldschmidt, and the mixture of cetyl dimethicone copolyol, polyglycerol isostearate (4 moles), and hexyl laurate sold under the name ABIL WE 09® by Goldschmidt, may be used. One or more co-emulsifiers may also be added, advantageously selected from the group comprising alkyl polyol esters.

[0177] We can also mention non-siliconized emulsifying surfactants, in particular alkyl esters or ethers of sorbitan, glycerol, polyol or sugars.

[0178] Examples of alkylated polyol esters include polyethylene glycol esters such as PEG-30 Dipolyhydroxystearate, such as the product marketed under the name Arlacel P135® by the company CRODA.

[0179] Examples of glycerol and / or sorbitan esters include polyglycerol isostearate, such as the product marketed under the name Isolan GI 34® by Goldschmidt; and sorbitan isostearate, such as the product marketed under the name Arlacel 987® by the company CRODA; sorbitan isostearate and glycerol, such as the product marketed under the name Arlacel 986® by the company CRODA, and mixtures thereof.

[0180] For O / W emulsions, examples of non-ionic emulsifying surfactants include polyoxyalkylated fatty acid and glycerol esters (more particularly polyoxyethylated and / or polyoxypropylated) such as polyethylene glycol and stearic acid ester with INCI name PEG-100 STEARATE marketed under the name Myrj SIOO-PA-(SG) by CRODA; oxyalkylated fatty acid and sorbitan esters; polyoxyalkylated fatty acid esters (in particular polyoxyethylated and / or polyoxypropylated) possibly in combination with a fatty acid and glycerol ester such as the PEG-100 Stearate / Glyceryl Stearate mixture marketed for example by CRODA under the name Arlacel 165; oxyalkylated fatty alcohol ethers (oxyethylenated and / or oxypropylenated); sugar esters such as sucrose stearate; fatty alcohol and sugar ethers,including alkyl polyglucosides (APGs) such as decyl glucoside and lauryl glucoside marketed for example by Henkel under the respective names Plantaren 2000® and Plantaren 1200®, cetostearyl glucoside possibly in mixture with cetostearyl alcohol, marketed for example under the name Montanov 68® by Seppic, under the name Tegocare CG90® by Goldschmidt and under the name Emulgade KE3302® by Henkel, as well as arachidyl glucoside, for example in the form of the mixture of arachidic and behenic alcohols and arachidyl glucoside marketed under the name Montanov 202® by Seppic. According to a particular embodiment of the invention, the mixture of the alkylpolyglucoside as defined above with the corresponding fatty alcohol can be in the form of a self-emulsifying composition, as described for example in document WO-A-92 / 06778.

[0181] As examples of anionic surfactants for making O / W emulsions, we can mention surfactants chosen from amino acids modified by at least one hydrocarbon chain in C8-C30, preferably in C8-C24, and their salts, in particular acyl glutamic acids (INCI name: acyl glutamic acid) or one of their salts (acyl glutamates), such as stearoyl glutamic acid or one of its salts, in particular sodium stearoyl glutamate (INCI name).

[0182] Such compounds are marketed under the name AMISOFT by the company AJINOMOTO and in particular under the references Amisoft CA, Amisoft LA, Amisoft HS 11 PF, Amisoft MK-11, Amisoft LK-11, Amisoft CK-11, or under the name EUMULGIN SG by the company COGNIS.

[0183] As anionic surfactants for making H / W emulsions, we can also mention hydrophobic modified polysaccharides, in particular inulins modified by hydrophobic chains such as alkylcarbamate groups, in particular alkyl C8-C18 carbamate, and more particularly laurylcarbamate.

[0184] As an example of these compounds, we can notably cite the product sold under the name INUTEC SL1 by the company CREACHEM.

[0185] The compositions according to the invention find their application in a large number of treatments, in particular cosmetic, of the skin, lips and hair, including the scalp, in particular for the protection and / or care of the skin, lips and / or hair, and / or for the makeup of the skin and / or lips.

[0186] Another object of the present invention is the use of the compositions according to the invention as defined above for the manufacture of products for the cosmetic treatment of the skin, lips, nails, hair, eyelashes, eyebrows and / or scalp, in particular skincare products, sun protection products and makeup products. EXAMPLES

[0187] The present invention will now be described more specifically by means of examples, which are in no way limiting of the scope of the invention. However, the examples allow for the support of specific features, variants, and preferred embodiments of the invention.

[0188] A- Examples of synthesis of merocyanins of formula (3) Example A1: Preparation of compound (14)

[0189] [Formula 14]

[0190] 122.23 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-l-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 75.45 grams of ethyl cyanoacetate in approximately equimolar proportions in the presence of a base and optionally a solvent.

[0191] The base / solvent combinations indicated in the following table are used. Example Base Solvent Example ALI DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)dimethylacetamide Example A 1.2 Triethylamine isopropanol Example A 1.3 3-methoxypropylamine isopropanol Example A 1.4 3-Methoxypropylamine tert-amyl alcohol Example A 1.5 3-Methoxypropylamine toluene Example A 1.6 3-Methoxypropylamine dimethylformamide Example A 1.7 Solvent-free 3-Methoxypropylamine Example A 1.8 N-Morpholine isopropanol

[0192] The completion of the alkylation reaction can be monitored, for example, by methods such as TLC, GC or HPLC. 162.30 grams of compound (14) are obtained in the form of a brown oil. After crystallization, the product is obtained in the form of yellowish crystals. Melting point: 92.7 °C. Example A2: Preparation of compound (15)

[0193] [Formula 15]

[0194] 101.00 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-l-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 86.00 grams of 2-cyano-N-(3-methoxy-propyl)-acetamide in approximately equimolar proportions in the presence of a base and optionally a solvent.

[0195] The base / solvent combinations indicated in the following table are used. Example Solvent Base Example A2.1 DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide Example A2.2 Triethylamine isopropanol Example A2.3 3-Methoxypropylamine isopropanol Example A2.4 3-Methoxypropylamine tert-amyl alcohol Example A2.5 3-Methoxypropylamine toluene Example A2.6 3-Methoxypropylamine dimethylformamide Example A2.7 3-Methoxypropylamine solvent-free

[0196] The crude product (15) is obtained in the form of a dark brown oil. After silica gel column chromatography (eluent: toluene / methanol 99 / 1), 81.8 grams of product were obtained in the form of yellowish crystals. Melting point: 84.7-85.3 °C. Example A3: Preparation of compound (27)

[0198] 13.09 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-l-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 10.12 grams of isobutyl cyanoacetate in the presence of a base and optionally a solvent.

[0199] The base / solvent combinations indicated in the following table are used. Example Solvent Base Example A3.1 DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide Example A3.2 Triethylamine isopropanol Example A3.3 3-Methoxypropylamine isopropanol Example A3.4 N-Methylmorpholine tert-amyl alcohol Example A3.5 3-Methoxypropylamine toluene Example A3.6 3-Methoxypropylamine dimethylformamide Example A3.7 Solvent-free 3-Methoxypropylamine

[0200] 15.97 grams of crude product (27) are obtained in the form of a dark brown oil. After silica gel column chromatography (eluent: toluene / acetone), 13.46 grams of product were obtained in the form of yellowish crystals. Melting point: 96.3 °C. Example A4: Preparation of compound (25)

[0201] [formula 25]

[0202]

[0203]

[0204]

[0205] 148.4 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-l-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 130.00 grams of 2-ethoxyethyl cyanoacetate in the presence of an organic base and a solvent. The base / solvent combinations indicated in the table below are used. Example Solvent Base Example A4.1 DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide Example A4.2 Triethylamine isopropanol Example A4.3 3-Methoxypropylamine isopropanol Example A4.4 N-Methylmorpholine tert-amyl alcohol Example A4.5 3-Methoxypropylamine toluene Example A4.6 3-Methoxypropylamine dimethylformamide Example A4.7 Solvent-free 3-Methoxypropylamine B- Example of synthesis of thiopyridinone compounds of formula (I) or (I') Step 1: Synthesis of compound 3 - N-[(2-thioxo-l,2-dihydropyridin-3-

[0206] yl)carbonyl]ethyl glycinate Route 1: via 2-mercaptonicotinic acid

[0207] Thionicotinic acid is introduced into a flask, followed by acetonitrile and then carbonyldiimidazole (CDI). The resulting mixture is heated under reflux for one hour and then left at room temperature. After returning to room temperature, ethyl glycinate hydrochloride is added and then the resulting mixture is heated again to a temperature of 60°C

[0208] for 3 hours. The mixture is then left at room temperature overnight. After the night, the reaction mixture is evaporated. The residue is resuspended in dichloromethane and washed twice with 2 N HCl. The organic phase is dried over anhydrous sodium sulfate then evaporated and purified over silica Dichloromethane 97 / methanol 3. The fractions are evaporated. A light yellow powder is obtained. Route 2: via 2-chlorotonic acid

[0209] In a three-necked flask, 2-chloronicotinic acid (250.0 g, 1.587 mol) is introduced into ethyl acetate (500 ml) and then SOC12 (210.0 g, 1.761 mol) is added dropwise into the mixture. The mixture is heated under reflux until complete conversion. Once the reaction is finished, the mixture is cooled to room temperature and diluted with ethyl acetate (375 ml). A solution of ethyl glycinate hydrochloride (265.8 g, 1.904 mol) diluted in water (400 ml) and triethylamine (393.5 g, 3.88 mol) is then added to the mixture. The mixture is stirred for 3 to 4 hours, and then the ethyl acetate is removed under vacuum. The aqueous solution thus obtained is then diluted with water (1250 ml) and then acidified with 3N HCl (25 ml). Sodium thiosulfate (1379g, 5.555mol) is then added and the mixture is heated under reflux for 6 hours. After cooling to 10°C, the yellow solid is filtered and washed with water (3 times 750ml). The raw product is then treated with carbon black in a 75 / 25 ethanol / water mixture. The carbon black is then hot-filtered and the ethanol is evaporated. The mixture is cooled to room temperature, then the product is filtered and vacuum-dried. A light yellow powder is thus obtained. The 1H NMR and mass spectra are consistent with the structure. Melting point: 151 °C (capillary tube).

[0210] Step 2: Synthesis of the compound N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]glycine from the compound obtained in step 1

[0211] In a three-necked bottle, ethyl N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]glycine nate (48 g, 0.317 mol) and a 95% EtOH solution (48 mL) are introduced. The resulting mixture is cooled to 10°C. A solution of NaOH (16 g) in 144 mL of water is added dropwise into the mixture. The organic solvent is evaporated and then the pH of the mixture is adjusted to a value of 3-4. The mixture is then cooled to a temperature between 0 and 10 °C and then filtered. The resulting product is washed with water and dried under vacuum. A light yellow powder is obtained. The 1H NMR and mass spectra are consistent with the structure. Melting point: 241.0-241.8 °C (capillary tube)

[0212] Example 2: Synthesis of compounds 1-1 and 1-2 Composed 1-1

[0213] In a 250 mL flask are introduced the (2-mercaptonicotinoyl)glycine obtained in example 1 (20.000 g, 1 Eq, 94.242 mmol) and DMF (100 mL). The mixture is stirred until a clear solution is obtained, then carbonyldiimidazole (16.809 g, 1.1 Eq, 103.67 mmol) is added per portion. The resulting suspension is stirred at a temperature of 20°C until no bubbling occurs (typically for one hour). Ethyl glycinate hydrochloride (14.470 g, 1.1 Eq, 103.67 mmol) is then added, and the mixture is stirred for one hour at a temperature of 20 °C. The reaction mixture is then slowly added to a 10% aqueous NaHCO3 solution while stirring. The resulting suspension is filtered through a sintered flask to obtain a solid, which is rinsed with distilled water. The solid is dried at 50 °C under vacuum to obtain ethyl (2-mercaptonicotinoyl)glycylglycinate (compound 1-1) as a yellow powder.

[0214] Spectroscopic analyses conform to the indicated structure. Compound 1-2

[0215] In a 250 mL flask, the compound 1-1, as obtained previously, (ethyl (2-mercaptonicotinoyl)glycylglycinate) (13.440 g, 1 Eq, 45.202 mmol) and distilled water (70 mL) are introduced. With stirring, a 50% sodium hydroxide solution is added until a pH value of around 12-13 is reached, maintaining the temperature below 25°C. The resulting mixture is stirred for one hour at a temperature of 25°C, then the pH is adjusted to a value of 2 with 37% hydrochloric acid. The resulting suspension is filtered through a sintered glass sinter and then the resulting solid is rinsed with distilled water. The solid is dried at 50 °C under vacuum to obtain the compound 1-2 (2-mercaptonicotinoyl)glycylglycine in the form of a yellow powder). C- Examples of solubilization

[0216] In these examples, the quantities of ingredients present in the compositions are given as % by weight of raw materials in relation to the total weight of the composition.

[0217] Examples 1 to 6: study of the solubility of compound 25 in the presence of compound 1-2

[0218] The following solutions were prepared at room temperature with different rates of the compound Thiopyridinone. Solution 1 2 3 4 5 6 Compound 1-2 0 0 1 2 5 10 pH adjustment (pH 6.2) Qs pH 5.5 Qs pH 5.7 Qs pH 5.8 Qs pH 5.5 Qs pH 5.7 Water Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100

[0219] Each of the solutions 1 to 6 was divided into 2 equal solutions, solutions 1' to 6' on the one hand, and solutions 1” to 6” on the other. Solutions 1' to 6' were kept as controls. In solutions 1" to 6", 2.5 g of compound 25 were added. They were then kept under magnetic stirring for 72 hours at room temperature, and then filtered with a 0.2 micron filter. An absorbance spectrum was obtained for each of the solutions 1' to 6' and 1" to 6" after dilution to the thousandth in distilled water while maintaining the pH of the solution, using a Carry 4000 instrument from the company Agilent, using a 2 mm thick quartz cuvette from the brand Starna. For each level of compound thiopyridinone 1-2, the spectrum of the solution of compound thiopyridinone 1-2 alone (solutions 1' to 6') is subtracted from that of the corresponding solution containing compound thiopyridinone 1-2 and compound 25 (solutions 1” to 6”). Results

[0220] The spectra obtained for solutions 1 and 2 show that the solubility of compound 25 does not depend on pH, between 6.2 and 5.5; The spectra obtained for solutions 2' to 6' and for solutions 2" to 6" show that the higher the concentration of thiopyridinone 1-2 in the solution, the greater the UV absorbance. An increase in absorption in the long UVA range is observed, linked to a higher concentration of compound 25 in the solution. Thus, we observe that when the level of compound thiopyridinone 1-2 increases, the amount of compound 25 that dissolves in water increases. By plotting the curve representing the absorption at 385 nm due to the presence of compound 25 in the solution as a function of the level of compound thiopyridinone 1-2, we obtain a straight line with the equation y = 0.0078x + 0.0331, with a correlation coefficient R2 = 0.9998. Thus, the compound thiopyridinone 1-2 improves the solubility of compound 25 proportionally. D- Illustrative examples

[0221] In these examples, the quantities of ingredients present in the compositions are given as % by weight of raw materials in relation to the total weight of the composition. Example 1 - essentially aqueous composition

[0222] The following composition was prepared. Phase Name INCI Composition per 100g Al WATER 63.7 Al 2-MERCAPTONICOTINOYL GLYCINE (compound 1-2) 1 A2 METHOXYPROPYLAMINO CYCLOHEXENYLIDE ENE ETHOXYETHYLCYANOACETATE (compound 25) 1 A3 DIPROPYLENE GLYCOL 20 A3 Preservative(s) 3.3 A3 POLYSORBATE 20 1 B ALCOHOL DENAT. 10 Operating procedure

[0223] Preparation of phase Al: introduce all the ingredients of phase Al into a beaker under magnetic stirring, heating to 75°C until a clear mixture is obtained. Add A2 to the beaker and let it stir for 5 minutes while maintaining the temperature at 75°C. Next, add all the ingredients of A3 to the beaker, while maintaining stirring and a temperature of 75°C for 15 to 20 minutes. The mixture will then be clear. Allow to return to room temperature before adding the ethanol from phase B.

[0224] 3 weeks after manufacture, the mixture remains clear and free of crystals.

[0225] Example 2 - composition in the form of an emulsion

[0226] The following composition was prepared. Phase Nom INCI Composition sur 100g Al WATER qs Al Glycol(s) 4 Al Agent(s) complexant(s) 0,3 A2 TEREPHTHALYLIDENE DICAMPHOR SULFONIC ACID (Mexoryl SX de Noveal) 0,33 A2 TRIETHANOL AMINE 0,17 A3 ACRYLATES COPOLYMER 2 A4 TRIETHANOL AMINE 0,79 B PENTAERYTHRITYL TETRA-DLT-BUTYL HYDROXYHY DROCINNAMATE (TINOGARD TT de BASF) 0,1 B Actif(s) 0,15 B DIETHYLAMINO HYDROXYBENZOYL HEXYL BENZOA TE (Uvinul A plus de BASF) 1 B BUTYL METHOXYDIBENZOYLMETHANE (Parsol 1789 de DSM Nutritional products) 2 B DROMETRIZOLE TRISILOXANE (Mexoryl XL de Novéal) 2 B BIS-ETHYLHEXYLOXYPHENOL METHOXYPHENYL TRI AZINE (Tinosorb S de BASF) 4,5 B ETHYLHEXYL TRIAZONE (UVINUL T150 de BASF) 4,8 B C12-22 ALKYL ACRYLATE / HYDROXYETHYLACRYLAT E 1 B DIISOPROPYL SEBACATE 7 B DIISOPROPYL ADIPATE 7 B C12-15 ALKYL BENZOATE 3 C ACRYLATES / C10-30 ALKYL ACRYLATE CROSSPOLYM ER 0,15 C SODIUM POLYACRYLATE 0,35 D 2-MERCAPTONICOTINOYL GLYCINE (composé 1-2) 0,5 D SODIUM THIOSULFATE 0,2 E Charge(s) 4,9 F Actif(s) 4 G ALCOHOL DENAT. 5 G METHOXYPROPYLAMINO CYCLOHEXENYLIDENE ETH OXYETHYLCYANOACETATE (compound 25) 1 I WATER 2.1 Operating procedure

[0227] Phase 1: Preparation of the aqueous phase (A) 1. Mixture A1: In a beaker, mix the ingredients of phase A1. Heat to 60°C with moderate stirring. Maintain the temperature and stirring until the ingredients are completely dissolved. 2. Addition of phases A2, A3 and A4: Maintain phase Al at 60°C and gradually add, under constant stirring, phases A2, A3, then A4. Ensure complete homogenization after each addition. Phase 2: Preparation of the oil phase (B) Mixture B: In a second beaker, mix all the ingredients of phase B. Heat the mixture to 75°C, with moderate stirring. Maintain the temperature and stirring until a homogeneous oily phase is obtained. Phase 3: Emulsification and successive additions Gradually pour the oily phase B into the aqueous phase while stirring constantly. Continue stirring for 10 minutes. Incorporate phase C into the emulsion, while continuing to stir. Incorporate the previously dissolved phase D. Mix until completely homogenized. Gradually add phase E while stirring. Incorporate phase F into the emulsion. Mix until homogenized. Next, add phase I while stirring. Cool the emulsion to 20°C with gentle stirring. Incorporate phase G into the emulsion cooled to 20°C. Mix until completely homogenized.

Claims

1. Demands Cosmetic or dermatological composition including: (a) at least one aqueous phase; (b) at least one merocyanin corresponding to the following formula (3), together with their isomeric geometric forms, in particular E / E or E / Z: in which: A is -O- or -NH; R is an alkyl group CrC22, an alkenyl group C2-C 22, a C2-C22 alcinyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups being able to be interrupted by one or more O groups; and (c) at least one compound selected from compounds of formula (I), tautomers of formula (!'), their salts, their solvates, such as their hydrates, their optical isomers, their racemates, and mixtures thereof: * H (D (O in which: - Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in C1-C10 or branched in C3-C10 optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and - R2 denotes a radical chosen from a) a hydrogen atom, b) a linear saturated hydrocarbon group in C1-C12 or branched in C3-C12 or cyclic in C3-C8 optionally substituted by one or more groups, which may be identical or different, chosen from i)

2. -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) an aryl group at C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals at Ci-C8> and c) an aryl group at C5-C12, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals at Ci-C8 and - R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-Ci0 or branched in C3-Ci0. Composition according to claim 1 wherein the merocyanins of formula (3) are selected from the following compounds, as well as their isomeric geometric forms, in particular E / E or E / Z: [h] 25 H ] 0 TT 2-ethoxyethyl (2Z)-cyano{ 3-[(3-methoxypropyl)a mino] cyclohex-2-en-1 -ylidene} ethanoate 27 1 1 0 1 H ] YY 2-methylpropyl (2Z)-cyano{3-[(3-methoxypropyl) amino]cyclohex-2-en-l-ylidene}ethanoate 29 1 CL 0^.

0. > H y TJ 2-butoxyethyl (2Z)-cyano{ 3-[(3-methoxypropyl)a mino] cyclohex-2-en-1 -ylidene} ethanoate 31 1 ] H ] TT 3-methoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino] cyclohex-2-en-1 -ylidene} ethanoate 37 1 ] HT ] TT 3-ethoxypropyl (2Z)-cyano{3-[(3-methoxypropyl) amino]cyclohex-2-en-l-ylidene}ethanoate Composition according to any one of claims 1 and 2 wherein the merocyanine of formula (3) is 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-l-ylidene}ethanoate (25) in its E / Z geometric configuration of the following structure:

3. and / or in its geometric E / E configuration of the following structure:

4. A composition according to any one of claims 1 to 3, wherein the merocyanins of formula (3) and / or their isomeric geometric forms are present in a concentration from 0.1% to 15% by weight, and preferably from 0.2% to 10% by weight. weight and even better from 0.5% to 5% by weight relative to the total weight of the composition.

5. Composition according to any one of claims 1 to 4 wherein Ri of formulas (I) and (!') represents a hydrogen atom; a linear alkyl group (in C1-C10) or a branched alkyl group (in C3-C10), in particular a linear alkyl group (in C1-C6) or a branched alkyl group (in C3-C6), such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl, in particular said alkyl group of Ri' is not substituted.

6. Composition according to any one of claims 1 to 5 wherein R2 of formulas (I) and (!') represents a hydrogen atom; a linear (C1-C10) or branched (C3-C10) alkyl group, in particular a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group of R2 not being substituted.

7. Composition according to any one of claims 1 to 6 wherein R3 of formulas (I) and (!') represents a hydrogen atom; a saturated linear C1-C10 or branched C3-C10 alkyl group; in particular a linear (Ci-C6) alkyl group or a branched (C3-C6) alkyl group, preferably a (C1-C4) alkyl group such as the methyl group.

8. Composition according to any one of claims 1 to 7 wherein R2 of formula (I) and (!') represents a linear (C1-C10) alkyl group or a branched (C3-C10) alkyl group, in particular a linear (C1-C6) alkyl group or a branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group being substituted by one or more groups selected from i), ii), iii) and iv) as defined in claim 1, preferably said alkyl group being substituted by one or two groups selected from i), ii) and iii), more preferably by one or two groups selected from i) and iii), better substituted by a group iii) such as the carboxy.

9. Composition according to any one of claims 1 to 8 wherein R2 of formulas (I) and (!') represents a cycloalkyl group (in C3-C8), preferably a cycloalkyl group (in C5-C7) such that cyclohexyl; an aryl group in C5-Ci2 optionally substituted by one or more hydroxyls and / or by one or more alkoxy radicals in Ci-C8, preferably a phenyl group in particular unsubstituted.

10. Composition according to any one of claims 1 to 9 wherein R3 of formulas (I) and (!') represents a hydrogen atom; a linear saturated alkyl group in Ci-Cio or branched in C3-CiO; in particular a linear alkyl group (in Ci-C6) or a branched alkyl group (in C3-C6), preferably an alkyl group (in CrC4) such as a methyl group.

11. Composition according to any one of claims 1 to 10 wherein: - Ri of formulas (I) and (!') represents a radical selected from a) a hydrogen atom, and b) a linear saturated CrC6 or C3-C6 branched alkyl group optionally substituted by one or more groups, which may be identical or different, selected from i) -O-R3, and ii) -S-R3, preferably optionally substituted by one or more i) groups;- R2 of formula (I) and (!') represents a radical chosen from a) a hydrogen atom, and b) a saturated hydrocarbon group linear in Ci-Cio or branched in C3-CiO or cyclic in C3-C8 as in C5-C6, optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a phenyl group optionally substituted by one or more hydroxyls and / or by one or more alkoxy radicals in Ci-C4 such as methoxy, preferably substituted by one or more groups selected from i) and iii), preferably iii) such as carboxy; and - R3 of formula (I) and (!') represents a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in C1-C6 or branched in C3-C6.;

12. Composition according to any one of claims 1 to 11 wherein: - Ri of formula (I) and (!') represents a radical selected from a) a hydrogen atom, and b) a linear saturated C1-C4 or branched C3-C4 alkyl group optionally substituted by one or more

13. groups, which may be identical or different, chosen from i) -OR3>plus preferably unsubstituted; - R2 of formula (I) and (!') represents a radical chosen from a) a hydrogen atom, and b) a linear saturated hydrocarbon group in C1-C10 or branched in C3-C10 or cyclic in C3-C8 as in C5-C6, optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, iii) -C(O)-O-R3, and iv) an aryl group in C5-C12, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in C1-C4; and - R3 of formula (I) and (!') represents a radical chosen from a) a hydrogen atom; b) a linear saturated alkyl group in C1-C4 or branched in C3-C4 such as methyl or ethyl. Composition according to any one of claims 1 to 12 wherein the compound of formula (I) is selected from the compounds 1 to 24 below, their tautomers, their salts, their solvates, such as their hydrates, their optical isomers, their racemates, and mixtures thereof, preferably compounds 1, 2, 4, 6, 7, 9, 11, 12, 14, 15, 16, 17, 18, 19, 20 or 21, more preferably 1, 9, 16, 18, 19, 20 or 21, even more preferably 18, 19, 20 or 21, and even better 20: No. Structure Chemical Name 1 H N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 2 \\ N-methyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 3 JH; N-octyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 4 N-benzyl-2-thio xo-l,2-dihydrop yridine-3-carbox amide 5 ■>--------> . ' X / / X / \ / \ / \\ 4.;....... / 1 w N-phényl-2-thio xo-l,2-dihydrop yridine-3-carbox amide 6 X '-*N '’ Xxx h N H N-cyclohexyl-2-t hioxo-l,2-dihydr opyridine-3-carb oxamide 7 <: çX X‘ X -x A K J çx? ~ N- [2- (4-méthoxy phényl)éthyl]-2-t hioxo-l,2-dihydr opyridine-3-carb oxamide 8 "7$ SK:- : : * H v^X N-(2-méthylprop yl)-2-thioxo-l,2-dihydropyridine-3-carboxamide 9 X 'X^ / •''jt*** XX XX N-pentyl-2-thiox o-l,2-dihydropy ridine-3-carboxa mide 10 Cl A _ T f "' N-nonyl-2-thiox o-l,2-dihydropy ridine-3-carboxa mide 11 ô / ( 5 / \ / 7 / / \ / N-(2-hydroxyéth yl)-2-thioxo-l,2-dihydropyridine-3-carboxamide 12 z>x / \ / Xm; Ü K i XX X» Xhs H N,N-diéthyl 2-m ercaptonicotinam ide 13 (VS^ Ü. k 'A'"' - <s n-éthyl-n-(2-hy droxyéthyl)-2-th ioxo-l,2-dihydro pyridine-3-carbo xamide 14 ..u-x-               -^'x    --^ n-(2,3-dihydrox ypropyl)-2-thiox o-l,2-dihydropy ridine-3-carboxa mide 15 j4x . a ah x' 'ax^''""'         x-x' n-(l,3-dihydrox ypropan-2-yl)-2-thioxo-l,2-dihyd ropyridine-3-car boxamide 16 x'"                       x^a---- n-[(2-thioxo-l,2 -dihydropyridin-3-yl)carbonyl]ala ninate d'éthyle17 1 J ■ .... ■Z*”''. N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]phenyl alaninate of ethyl 18 XXv^s N-methyl-N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 19 _^'x A7x N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]ethyl glycine 20 XL ,® a « N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]glycine 21 o=f « \— fi N-methyl-N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]glycine 22 *vK / \Z\. N,N-bis(2-hydro xyethyl)-2-thiox ol,2-dihydropyridine-3-carboxa mide 23 .^X x'X z\ N-(3-methoxypr opyl)-2-thioxo-l, 2-dihydropyridine e-3-carboxamide 24 N-butyl-2-thioxo -1,2-dihydropyridine-3-carboxam ide

14.

15.

16. A composition according to any one of claims 1 to 13, wherein said compound of formula (I) or (!') is present in the composition in a concentration from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight, more preferably from 0.1% to 3% by weight, relative to the total weight of the composition. A composition according to any one of claims 1 to 14 further comprising one or more additional UV filters. Use of at least one compound selected from the compounds of formula (I), the tautomers of formula (!'), their salts, their solvates, such as their hydrates, their optical isomers, their racemates as defined in any one of claims 1 and 5 to 13 for solubilizing a merocyanin as defined in any one of claims 1 to 3 in aqueous phase.< / s>